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why anyone ever thought they could make meaningful money from enabling the formerA better question might be why buyers thought it was worth paying for that "advantage" you want explained. When buyers think a thing like that, someone will fulfill their ask.
If LLMs are eating the revenue stream, that likely gives the answer:
Buyers thought Tailwind meant they didn't have to learn or do a thing in order to achieve an outcome. And someone built a niche around that.
Is it true, and if not, why does it persist? Also not hard to explain given today's approaches to learning and the abysmal state of the ad delivery sites that used to be web search.
It's almost impossible today to find the very few sites that show the standard component lib rendered as web components with modern CSS as supported cross browser -- no single party stands to profit from making that case. You'll see it in parts from other frameworks that aren't trying to do the UI saying "our framework drives native HTML/CSS/JS/WASM" with a few examples, but that's surprisingly unlikely to find from Google with "How do I make my web app look good?" if you don't know which terms to use.
One could probably make a niche living giving modern web-native training for corporates. (Plenty firms purport to offer this, but generally don't really teach past the days of bootstrap.) Price against their recurring licensing costs, and a $10K to $30K class (the type enterprise SaaS products like Hashicorp offers for e.g. Terraform ecosystem) for modern web might even pay better than Tailwind.
Generally, though, arbitrage plays can't be expected to last unless the value-add is actual work others don't want to do, so business model decay is likely to happen to things like Tailwind that have their ideas become standards that get implemented by the browser industry (see Apple and "Sherlocking": https://appdevelopermagazine.com/sherlocked:-the-controversi...